It looks to me like the wedge just got drilled off angle. I'd just file it down. Better yet, head out to the LBS and look for a used wedge. It's not like it's a precision machined part.
One thing that I noticed from all of your pictures is no grease on your stems. Maybe you just cleaned it off for the pictures, but those stems need lots of grease. Make sure to get plenty in the angled space between the stem and the wedge and cover the wedge as completely as you can. Wedges are just cheapo steel castings that are drilled and tapped. If you don't grease them they will rust and often get severely stuck. Unthread the wedge and make sure you get a good dollop of grease on the bolt threads. Also, make certain to get the contacting surfaces of the stem and the wedge well greased so they can slide against each other.
In your original post you say that the stem is rocking from side to side. I would not believe that is the stem. That's the headset. If the stem is rocking, then there has to be some gap between the outside surface of the stem and the inside surface of the headset bearing race. These should fit very closely. Get some calipers and measure. They should be within 0.5mm or less. If they don't then there is a mismatch and your handlebars will rock. How the quill&wedge are seated have nothing to do with that. Did you buy this bike new? If not, it's possible that the stem got replaced at some point and they installed one with the wrong O.D. and did not properly match it to the headset. You could install a shim in there to stop the movement. It's better to get a stem and headset that match properly.